3-Heptanone

3-Heptanone
Names
IUPAC name
Heptan-3-one
Other names
Ethyl butyl ketone
3-Oxoheptane
Butyl ethyl ketone
Identifiers
3D model (JSmol)
506161
ChEBI
ChemSpider
ECHA InfoCard 100.003.081
EC Number 203-388-1
MeSH 3-Heptanone
RTECS number MJ5250000
UN number 1224
Properties
C7H14O
Molar mass 114.19 g·mol−1
Appearance Colorless liquid
Odor powerful, fruity[1]
Density 0.812 g cm−3
Melting point −39 °C (−38 °F; 234 K)
Boiling point 146 to 149 °C (295 to 300 °F; 419 to 422 K)
1% (20 °C)[1]
Vapor pressure 4 mmHg (20 °C)[1]
Hazards
Safety data sheet [2]
R-phrases (outdated) R10, R22
S-phrases (outdated) S23
Flash point 41 °C (106 °F; 314 K)
Lethal dose or concentration (LD, LC):
2760 mg/kg (rat, oral)[3]
US health exposure limits (NIOSH):
PEL (Permissible)
 TWA 50 ppm (230 mg/m3)[1]
REL (Recommended)
 TWA 50 ppm (230 mg/m3)[1]
IDLH (Immediate danger)
 1000 ppm[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references


3-Heptanone (butyl ethyl ketone), is a seven carbon ketone. It is a colorless liquid with a "green odor," also described to have a fruity scent. It is often used as a perfume/fragrance, as a solvent for cellulose, nitrocellulose, or vinyl resins, and as a synthetic building block in the preparation of other organic molecules.[4]

Preparation

3-Heptanone is produced industrially through reductive condensation of propionaldehyde (propanal) with butanone (methyl ethyl ketone). This reaction yields hept-4-en-3-one, which is subsequently hydrogenated to 3-heptanone.

CH
3CH
2CHO   +   CH
3C(O)CH
2CH
3   →   CH
3CH
2C(O)CHCHCH
2CH
3   +   H
2O
CH
3CH
2C(O)CHCHCH
2CH
3   +   H
2   →   CH
3CH
2C(O)CH
2CH
2CH
2CH
3

References

  1. 1 2 3 4 5 6 "NIOSH Pocket Guide to Chemical Hazards #0266". National Institute for Occupational Safety and Health (NIOSH).
  2. ↑ http://www.chemicalbook.com/ProductMSDSDetailCB0852672_EN.htm External MSDS
  3. ↑ "Ethyl butyl ketone". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  4. ↑ Siegel, Hardo; Eggersdorfer, Manfred (2012). "Ketones". Ullmann's Encyclopedia of Industrial Chemistry. 20. p. 195. doi:10.1002/14356007.a15_077.
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